(4-Carboxybutyl)triphenylphosphonium bromide → HCID 86757097, compound

HRID 1383281Notes

Reaction equation

HRID 1383281 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].O[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](=O)[CH3:39]>O1CCCC1>[CH3:39]/[C:38](/[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH3:29])=[CH:8]/[CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 11344448HCID 11344448, compound

Product 1

HCID 86757097HCID 86757097, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

164.6 g (0.37 mol) of (4-carboxybutyl)triphenylphosphonium bromide were suspended in 700 ml of tetrahydrofuran. 101 g (0.9 mol) of potassium t-butylate in 150 ml of tetrahydrofuran were added and then 68 g (0.36 mol) of 11-hydroxy-2-undecanone in 50 ml of tetrahydrofuran were added After usual working up there were obtained 98 g of crude 5Z-6-methylpentadec-5-enoic acid.

Sources & evidence

ORD record
ord-787957dcabd74079aa945a7e3ffb6fdc
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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